Cariporide | CAS#159138-80-4 | NHE1 inhibitor

Cariporide
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 563402

CAS#: 159138-80-4

Description: Cariporide is a selective Na+/H+ exchanger isoform 1 (NHE1) inhibitor.

Chemical Structure

Cariporide

CAS# 159138-80-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 563402
Name: Cariporide
CAS#: 159138-80-4
Chemical Formula: C12H17N3O3S
Exact Mass: 283.10
Molecular Weight: 283.340
Elemental Analysis: C, 50.87; H, 6.05; N, 14.83; O, 16.94; S, 11.31

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 230
10mg	USD 380
50mg	USD 840
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Cariporide; HOE642; HOE-642; HOE 642;

IUPAC/Chemical Name: N-(Diaminomethylidene)-3-methylsulfonyl-4-propan-2-ylbenzamide

InChi Key: IWXNYAIICFKCTM-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H17N3O3S/c1-7(2)9-5-4-8(11(16)15-12(13)14)6-10(9)19(3,17)18/h4-7H,1-3H3,(H4,13,14,15,16)

SMILES Code: O=C(/N=C(N)\N)C1=CC=C(C(C)C)C(S(=O)(C)=O)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Cariporide (HOE-642) is a selective Na+/H+ exchange inhibitor.
In vitro activity:	Cariporide significantly decreased NHE1 expression in breast cancer cells (Fig. (Fig.2e,2e, f), where it inhibited the proliferation of MCF-7 and MCF-7/ADR cells in a dose- and time- dependent manner, as assessed by CCK8 assays with a range of concentrations (Fig. (Fig.2a),2a), of doxorubicin (Fig. (Fig.2b)2b) or paclitaxel (Fig. (Fig.2c)2c) in culture for 24 and 48 h. In addition, after cotreatment with cariporide and doxorubicin, the IC50 value decreased to 17.16 ± 0.06 μg/ml(2.463-fold), which was significantly lower than in cells treated with doxorubicin only. The same results were observed in the paclitaxel-only and cotreatment groups (Fig. (Fig.2c,2c, d). These results suggest that cariporide can sensitize drug-resistant cells to chemotherapeutic drugs after the cotreatment with cariporide and doxorubicin or paclitaxel. Reference: BMC Cancer. 2019 Mar 8;19(1):211. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30849956/
In vivo activity:	After continuous intraperitoneal injection of cariporide (3 mg/kg) for 7 days, the body weight and behavior of nude mice showed no significant toxic effects. However, cariporide significantly retarded the growth of tumors in vivo (Fig. (Fig.4e).4e). The tumor volumes and weights significantly decreased in the two cariporide-treated groups compared to the other assayed groups (Fig. (Fig.4f,4f, g). In detail, no significant difference in the body weight of each group was detected initially, but decreases in body weight were observed 15 days after administration, and even the control group and single ADR group were significantly lower on day 21 (Fig. (Fig.4f).4f). These data suggest that NHE1 is an upstream effector of the process of cariporide-induced inhibition of breast cancer cell proliferation. Collectively, cariporide inhibited the growth of implanted breast cancer and increased its sensitivity to doxorubicin in nude mice. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30849956/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	87.0	307.04

Preparing Stock Solutions

The following data is based on the product molecular weight 283.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:	1. Chen Q, Liu Y, Zhu XL, Feng F, Yang H, Xu W. Increased NHE1 expression is targeted by specific inhibitor cariporide to sensitize resistant breast cancer cells to doxorubicin in vitro and in vivo. BMC Cancer. 2019 Mar 8;19(1):211. doi: 10.1186/s12885-019-5397-7. PMID: 30849956; PMCID: PMC6408845. 2. Teshima Y, Akao M, Jones SP, Marbán E. Cariporide (HOE642), a selective Na+-H+ exchange inhibitor, inhibits the mitochondrial death pathway. Circulation. 2003 Nov 4;108(18):2275-81. doi: 10.1161/01.CIR.0000093277.20968.C7. Epub 2003 Oct 20. PMID: 14568900.
In vivo protocol:	1. Chen Q, Liu Y, Zhu XL, Feng F, Yang H, Xu W. Increased NHE1 expression is targeted by specific inhibitor cariporide to sensitize resistant breast cancer cells to doxorubicin in vitro and in vivo. BMC Cancer. 2019 Mar 8;19(1):211. doi: 10.1186/s12885-019-5397-7. PMID: 30849956; PMCID: PMC6408845. 2. Albatany M, Li A, Meakin S, Bartha R. In vivo detection of acute intracellular acidification in glioblastoma multiforme following a single dose of cariporide. Int J Clin Oncol. 2018 Oct;23(5):812-819. doi: 10.1007/s10147-018-1289-0. Epub 2018 May 10. PMID: 29749579.

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2: Verma V, Bali A, Singh N, Jaggi AS. Implications of sodium hydrogen exchangers in various brain diseases. J Basic Clin Physiol Pharmacol. 2015 Sep;26(5):417-26. doi: 10.1515/jbcpp-2014-0117. Review. PubMed PMID: 26020555.

3: Chang HB, Gao X, Nepomuceno R, Hu S, Sun D. Na(+)/H(+) exchanger in the regulation of platelet activation and paradoxical effects of cariporide. Exp Neurol. 2015 Oct;272:11-6. doi: 10.1016/j.expneurol.2014.12.023. Epub 2015 Jan 13. Review. PubMed PMID: 25595121; PubMed Central PMCID: PMC4500746.

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6: Harguindey S, Arranz JL, Polo Orozco JD, Rauch C, Fais S, Cardone RA, Reshkin SJ. Cariporide and other new and powerful NHE1 inhibitors as potentially selective anticancer drugs--an integral molecular/biochemical/metabolic/clinical approach after one hundred years of cancer research. J Transl Med. 2013 Nov 6;11:282. doi: 10.1186/1479-5876-11-282. Review. PubMed PMID: 24195657; PubMed Central PMCID: PMC3826530.

7: Madonna R, De Caterina R. Sodium-hydrogen exchangers (NHE) in human cardiovascular diseases: interfering strategies and their therapeutic applications. Vascul Pharmacol. 2013 Nov-Dec;59(5-6):127-30. doi: 10.1016/j.vph.2013.10.001. Epub 2013 Oct 15. Review. PubMed PMID: 24140414.

8: Madonna R, Cevik C, Nasser M. Electrical plasticity and cardioprotection in myocardial ischemia--role of selective sodium channel blockers. Clin Cardiol. 2013 May;36(5):255-61. doi: 10.1002/clc.22113. Epub 2013 Mar 25. Review. PubMed PMID: 23529949.

9: Karmazyn M. NHE-1: still a viable therapeutic target. J Mol Cell Cardiol. 2013 Aug;61:77-82. doi: 10.1016/j.yjmcc.2013.02.006. Epub 2013 Feb 18. Review. PubMed PMID: 23429008.

10: Avkiran M, Cook AR, Cuello F. Targeting Na+/H+ exchanger regulation for cardiac protection: a RSKy approach? Curr Opin Pharmacol. 2008 Apr;8(2):133-40. doi: 10.1016/j.coph.2007.12.007. Epub 2008 Jan 28. Review. PubMed PMID: 18222727.

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12: Baartscheer A. Chronic inhibition of na(+)/h(+)-exchanger in the heart. Curr Vasc Pharmacol. 2006 Jan;4(1):23-9. Review. PubMed PMID: 16472174.

13: Lee C, Dhalla NS, Hryshko LV. Therapeutic potential of novel Na+-Ca2+ exchange inhibitors in attenuating ischemia-reperfusion injury. Can J Cardiol. 2005 May 1;21(6):509-16. Review. PubMed PMID: 15917880.

14: Moens AL, Claeys MJ, Timmermans JP, Vrints CJ. Myocardial ischemia/reperfusion-injury, a clinical view on a complex pathophysiological process. Int J Cardiol. 2005 Apr 20;100(2):179-90. Review. PubMed PMID: 15823623.

15: Pisarenko OI. [Na+/H+ exchange inhibitors: a new class of cardioprotectors]. Ross Fiziol Zh Im I M Sechenova. 2004 Sep;90(9):1103-12. Review. Russian. PubMed PMID: 15559784.

16: Reffelmann T, Kloner RA. Microvascular alterations after temporary coronary artery occlusion: the no-reflow phenomenon. J Cardiovasc Pharmacol Ther. 2004 Sep;9(3):163-72. Review. Erratum in: J Cardiovasc Pharmacol Ther. 2004 Dec;9(4):following 289. Reffemann, Thorsten [corrected to Reffelmann, Thorsten]. PubMed PMID: 15378136.

17: Bolli R, Becker L, Gross G, Mentzer R Jr, Balshaw D, Lathrop DA; NHLBI Working Group on the Translation of Therapies for Protecting the Heart from Ischemia. Myocardial protection at a crossroads: the need for translation into clinical therapy. Circ Res. 2004 Jul 23;95(2):125-34. Review. PubMed PMID: 15271864.

18: Kloner RA, Rezkalla SH. Cardiac protection during acute myocardial infarction: where do we stand in 2004? J Am Coll Cardiol. 2004 Jul 21;44(2):276-86. Review. PubMed PMID: 15261919.

19: Moukarbel GV, Ayoub CM, Abchee AB. Pharmacological therapy for myocardial reperfusion injury. Curr Opin Pharmacol. 2004 Apr;4(2):147-53. Review. PubMed PMID: 15063358.

20: Linz WJ, Busch AE. NHE-1 inhibition: from protection during acute ischaemia/reperfusion to prevention/reversal of myocardial remodelling. Naunyn Schmiedebergs Arch Pharmacol. 2003 Oct;368(4):239-46. Epub 2003 Sep 19. Review. PubMed PMID: 14504689.

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